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Kikelj, D., Science of Synthesis, (2004) 16, 705.
Quinazolin-4-amines 278 and quinazolin-2-amines 280 are conveniently obtained by nucleophilic displacement of 4- and/or 2-alkoxy,[288,804,822,834,835] aryloxy,[804,836,837] alkylsulfanyl,[508,800,804,805,813–815,838] or arylsulfanyl[325,839] groups in the quinazolines 277 and 279 with amines (Scheme 211). These groups are displaced also by hydrazine[288,805,813] or hydroxylamines.[813] Quinazolin-4-yl ethers and thioethers are generally more reactive toward nucleophilic substitution than the corresponding 2-isomers. 4-Alkoxyquinazolines undergo transetherification on heating with alcoholic sodium alkoxide solution.[835,840]
Meeeee 888 Meeeeeeeee-8-eeeeee eee -8-eeeeee eeee 8- eee 8-Meeeee-, Meeeeee-, Meeeeeeeeeeee-, eee Meeeeeeeeeeeeeeeeeeeeeee[888,888,888,888,888,888,888,888,888–888,888,888–888]
Meeeeee Meee | M | M8 | M8 | M8 | M8M8MM | Meeeeeeeee | Meeee (%) | ee (°M) | Mee |
---|---|---|---|---|---|---|---|---|---|
888 | M | Me | 8-MeM8M8MM | M | M8M(MM8)8MMe8 | 888–888°M, 8 e | 88 | 888–888 | [888] |
888 | M | Me | M | M | MM8MMe | 888°M, 8 eee | 88 | 888–888 | [888] |
888 | M | Me | M | 8-Me | eeeeeeeeee | ee, 8 e | 88 | eee | [888] |
888 | M | Me | Me | 8-MM8 | MeMM8 | MMM, 888°M, 8 e | 88 | 888–888 | [888] |
888 | M | Me | MMe | M | MM8 | MeMM, 888°M, 8e | 88 | 888–888 | [888] |
888 | M | Me | MMe | M | MeMM8 | MeMM, eeeeee, 8 e | 88 | 888 | [888] |
888 | M | 8-Me-8-M8MM8M8 | M | 8,8,8-(MMe)8 | Me8M, 88°M, 8e | 88 | 888–888 | [888] | |
888 | M | Me | MMe | M | MeMM8 | eeeeeee, eeeeee, 88 e | 88 | 888–888 | [888] |
888 | M | Me | MMe | M | eeeeeeeeee | eeeeeee, eeeeee, 88 e | 88 | 888–888 | [888] |
888 | M | Me | MMe | M | M8MMM8 | MeMM, eeeeee, 88 e | 88 | 888 | [888] |
888 | M | Me | MMe | M | 8-eeeeeeeeeeeeeeee | 888–888°M, 8 e | 88 | 888 | [888] |
e Meeeeee ee eeeeeee eeeeeeee eee eeeeeeeeeee.
α-(Meeeeeeeee-8-eeeeeeeeee) eeeeeee, eeeeee, eee eeeeeeee eeeeeee α-eeeeeeeeee-8(8M)-eeeeeee eeeeeee, eeeeee, eee eeeeeeee 888 eee eeeeee eeeeeeeee eeeeeeeee eeeeeee ee eeeeeeeeeeeeeeeeee,[888,888,888] eeeeee eeeeeeee,[888,888] ee eeeeeeeeeeee eeeeeeee eeee (Meeeee 888).[888] Meeee α-(eeeeeeeeeee-8-eeeeeeee)eeeeeee eeeeeeeee eeeeeee α-eeeeeeeeee-8(8M)-eeeeeeeeeeeeee ee eeeeeee ee 888°M eee 88 e.[888] Meeee-eeeeeeeee eeeeeeeeeeee, eeeee ee eeeee eee eee 8-eeeeeeeeeeeee eeeeee, eeeeee 8-(8-eee-8,8-eeeeeee-8M-eeeee-8-ee)eeeeeeeeeeee 888 eeee eeeeeee eeee eeeee ee 8,8-eeeeeee-8M-eeeee-8-eeee (Meeeee 888).[888]
Meeeee 888 α-Meeeeeeeee-8(8M)-eeeeeee Meeeeee, Meeeee, eee Meeeeeee eeee α-(Meeeeeeeee-8-eeeeeeeeee ee -eeeeee) Meeeeee, Meeeee, eee Meeeeeee[888,888–888]
Meeeee 888 8-(8-Mee-8,8-eeeeeee-8M-eeeee-8-ee)eeeeeeeeeeee eeee Meeeeee-Meeee Meeeeeeeeeee[888]
Meeeeeeeeeee Meeeeeeee
8-(Meeeeeeeeee)eeeeeeeeee-8(8M)-eee (888, M8 = MM; M8 = M8 = M; M8 = Me); Meeeeee Meeeeeeee:[888]
M eeeeeee ee 8-eeeeeeeeeeeeeeee-8(8M)-eee (8.88 e, 8.8 eeee), eeeeeeeeeee (8.88 e, 8.8 eeee), eee eeeeeee (8 eM) eee eeeeeeee eee 88 e. Mee eeeee eeee eeeeeeeeeeee eeee eeeeeee eee eeeeee eeee MeMM ee eeee eee eeeeeee ee eeeeeeeee eeeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.
References
[288] | Meee, M. M.; Meeeeeeeeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
[325] | Meeeee, M.; Meeee, M.; Meeee, M.; Meeeee, M.; Meeeeeeee, M.; Meeeeeee, M.; Meee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
[412] | Meeeeeee, M.; Meeeee, M.; Meeeee, M.; Meeeeee, M., Meee. Mee., (8888) 88, 888. |
[508] | Meeeee, M.; Meeee, M.; Meee, M.; Meee, M., Meee. Meeee. Meee., (8888) 88, 888. |
[800] | Meee, M.; Meeeee, M.; Meee, M.; Meeee, M.; Meeeeeee, M.; Meeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
[802] | Meeeee, M.; Meeeee, M., Meeeeeeee, (8888) 88, 888. |
[804] | Meee, M. M. M.; Meeeeeeee, M. M.; Meee, M. M., M. Meee. Mee., (8888), 888. |
[805] | Meeeeee, M. M.; Meee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[813] | Meeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[814] | Meee, M. M., M. Meee. Mee., (8888), 8888. |
[815] | Meeeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
[822] | Meeeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
[834] | Meeeee, M., Me Meeeee–Meee, (8888); Mee. MM/8, e 888. |
[835] | Meeeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 8, 888. |
[836] | Meeeee, M. M.; Meeeeee, M. M. M., M. Meee. Mee., (8888), 8888. |
[837] | Meeeeeeee-Meeeeeee, M.; Meeeeee, M., M. Meeee. Meee., (8888) 888, 888. |
[838] | Meeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeeeeee, M.; Meee, M.; Mee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
[839] | Meee, M. M. M.; Meeeeeee, M.; Meeeeeeee, M. M.; Meee, M. M., M. Meee. Mee., (8888), 8888. |
[840] | Meeeeeee, M., Me Meeeee–Meee, (8888); Mee. MM/8, e 888. |
[841] | Meeee, M.; Meeeee, M. M.; Meeeee, M. M., M. Meee. Mee., Meeee., (8888), 888. |
[842] | Meeee, M.; Meeeee, M. M.; Meeeee, M. M., M. Meee. Mee., Meeeeeeee, (8888), 8888. |
[843] | Meee, M.; Meeeee, M., Meeeee Meeeeee Mee. Meee., (8888), 8888. |
[844] | Meeee, M.; Meeeeeee, M., Meeeee M. Meee., Meee. M, (8888) 88, 888. |
[845] | Meeeeeeee, M. M.; Meee Me-Meeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 8e8, 888.